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In July 2010, amidst continued fall-out from the Great Recession, the New York Times published a front-page story about an unemployed college graduate living with his parents in a Boston suburb who’d just turned down a $40,000-a-year job as an insurance claims adjustor.

“I am absolutely certain that my job hunt will eventually pay off,” said 24-year-old Scott Nicholson, a Colgate University honors graduate with a degree in political science, explaining his decision to hold out for something better even after two years of fruitless searching.

The piece quickly became notorious, setting off a tsunami of online comments—1,487 at last count—the vast majority expressing outrage at what readers perceived as an absurd sense of entitlement enabled by a too-indulgent family.

“Turning down a job for $40,000 a year after graduating from a second tier (at best) school because he is too good for the position? The kid deserves whatever hardship he endures,” was one typically harsh response.

I recently thought back to this article—and the heated debate that ensued—when I got a call from a friend who heads up a big department of a big organization. She’d read some of my posts about the challenges of looking for work after the Great Recession and wanted to share her own quite different perspective.

I have to say I found this fascinating. And while it was (and is) hard for me to believe that the situation for employers is really quite so bleak, I did start to notice other signs of similar frustration. For example this plaintive tweet from a local tech entrepreneur, formerly of Microsoft: “Why do so few job applicants bother to follow up? And some of the best cover letters don’t even show up for interviews.”

The more I thought about it, the more convinced I became that such behaviors, along with the resulting frustration, can be traced to a profound confusion about what work is and is not, as well as what it should be—a confusion now thrown into relief by the stressor of hard times.

It’s not news that the so-called millennials—the cohort now entering the workforce—grew up with extraordinary expectations fueled by Baby Boomer parents who encouraged them to dream big. Further feeding such attitudes was the Oprah-fication of American popular culture along with self-help classics such as Do What You Love and the Money Will Follow and the mega-bestseller The Secret, which posits a “law of attraction” that allows each of us to “manifest” our desires. Even the popular maxim that “anyone can be president” (never mind the nation’s declining place on social mobility measures) can be traced to this cultural strand.

At the same time, our nation is deeply rooted in the Puritan work ethic, with its emphasis on frugality, discipline, and self-reliance. Such teachings have been with us from early days, finding expression in the best-selling writings of Benjamin Franklin up on through present-day political rhetoric. (Think Mitt Romney’s tireless if problematic claims of being a self-made man.)

That millennials are struggling should come as no surprise, given these exacting and often conflicting cultural expectations. Those of us who came of age in the Boom Years may have managed to bridge the two. But when money is scarce and jobs are few (Hello, New Normal!), this is no easy feat.

So what’s a millennial supposed to do? Presented with conflicting absolutes, how are they supposed to choose?

This is precisely the sort of dilemma considered by Harvard psychologist Robert Kegan in In Over Our Heads: The Mental Demands of Modern Life. As Kegan sees it, we live in an age where demands are many and often at odds, and guidelines for choosing between them are scarce. At the same time, relatively few of us are sufficiently grounded in our own beliefs to stand up to social pressures and chart an independent course—to be what Kegan calls “self authoring.” That’s not such a big problem when society’s expectations are consistent. But when a culture makes the sort of conflicting demands that ours routinely does, things can turn ugly very quickly.

Which is where many millennials find themselves right now: Wanting to do the Right Thing but without a way to decide what that right thing is. Where is the line between self-confidence and entitlement? Where is the line between admirable risk-taking and foolish behavior? Where is the line between being responsible and giving up?

Depending on whom a millennial asks, they’re likely to get different answers, and regardless of which one they choose, they’re likely to find themselves at odds with someone whose opinion they value. There may not be much that we can do right now to change this cultural context. What we can do is to acknowledge that Scott Nicholson and other millennials have good reason to feel dazed and confused.

Edited 3/15/12: Various non-substantive revisions for style and clarification.

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About Me

Amy Gutman is a writer and lawyer with eclectic interests and a resume to match. Her work has appeared in the New York Times, Salon, the Chicago Tribune, and Psychology Today, among other venues, and she is the author of two suspense novels, both published by Little, Brown.She lives and works in Boston, in the heart of Plan B Nation.